595552-64-0Relevant academic research and scientific papers
Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones
Taguri, Tomonori,Yamakawa, Rei,Fujii, Toru,Muraki, Yuta,Ando, Tetsu
, p. 852 - 858 (2012)
All four of the possible stereoisomers of 5,9-dimethylheptadecane, the major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella), were synthesized by the coupling of two chiral blocks with a methyl branch at the 2- or 3-position. The blocks were prepared by applying the stereospecific inversion of secondary tosylates, which were derived from (R)- and (S)-propylene oxide, and their enantiopurities were confirmed by chiral HPLC analysis.
Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer
Taguri, Tomonori,Yaginuma, Katuhiko,Yamamoto, Masanobu,Fujii, Toru,Ando, Tetsu
, p. 761 - 765 (2015/07/20)
All four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component of the apple leafminer (Lyonetia prunifoliella: Lepidoptera), were synthesized starting from (R)- and (S)-propylene oxide by applying stereospecific inversion of chiral secondary tosylates as a key step. Field evaluation showed that male moths of the Japanese population were selectively attracted by the (10S,14S)-isomer and that the activity was not inhibited by the enantiomer.
Nucleophilic displacement reactions in ionic liquids: Substrate and solvent effect in the reaction of NaN3 and KCN with alkyl halides and tosylates
Chiappe, Cinzia,Pieraccini, Daniela,Saullo, Paola
, p. 6710 - 6715 (2007/10/03)
Room-temperature ionic liquids have been used as environmentally benign solvents for the preparation of primary and secondary alkyl azides and nitriles under solid-RTIL phase-transfer conditions. The reaction of primary, secondary, and tertiary halides or tosylates with KCN and NaN3 has been investigated in three ionic liquids ([bmim][PF6], [bmim][N(Tf) 2], and [hpyr] [N(Tf)2]). The observed nucleofugacity scales for the reaction of NaN3 are similar to those reported for the same process in cyclohexane, indicating that in these solvents it is possible to evidence the intrinsic ability to depart of leaving groups. Changes in the nature of the IL cation or anion determine significant modifications in reactivity of the investigated substrates. Reactivity has been interpreted considering a gradual shift of the mechanism from concerted SN2 (primary substrates) to stepwise SN1 (tertiary substrate, 3), through the nucleophilically assisted formation of an ion pair intermediate, in the case of 2d.
